High-molecular fatty acid containing arsenic.



UNITED STATES PriIENT OFFICE.

EMIL FISCHER, OF BERLIN, GERMANY, ASSIGNOR TO FARBENFABRIKEN VORM.

FRIEDR. BAYER & CO., 0F ELBERFELD, GERMANY, A CORPORATION OF GER-HIGI-I-MOLECULAR FATTY ACID CONTAINING ARSENI'C.

Patented Dec. 30, 1 913.

MANY.

1,082,509. Specification of Letters Patent.

N0 Drawing. Application filed August 27, 1912- Serial N0. 717,247.

To all whom it may concern Be it known that I, EMIL FIsoHER, doctor ofphilosophy, professor of chemistry, citi-' the property hitherto not yetobserved that on being heated with the halogen compounds of arsenic theycombine with these products. On using for this reaction high molecularsubstances, such as stearolic acid (C H OQ or behenolic acid (C H Oproducts similar to fats are obtained which are absorbed in thedigestive organs and appear therefore to be valuable for therapeuticpurposes.

'The products thus obtained contain in addition to arsenic, halogen in aquantity approximately equivalent to the amount of arsenic. They arebrownish semi-fluid compounds insoluble in water and soluble in alcohol.They are acidsand form soluble alkali salts and insoluble calcium andstrontium salts.

In order to illustrate the new process more fully the following examplesare given, the parts being by weight Example 1: 2 parts of stearolicacid and 3 parts of arsenic trichlorid (Ascl are heated in a closedvessel for 6 hours to 140 C. The product of the reaction is a brown oilysubstance from which unchanged AsCl can be removed by distillation incacao or more conveniently inthe following ways: The product of thereaction is dissolved in ether and shaken repeatedly with water whichtreatment results in the separation of.

arsenic trioxid. The ethereal solution is carefully concentrated andpoured into a normal potash solution cooled by ice that a clear solutionresults. After a few minutes the resulting solution is acidulated withdilute hydrochloric acid, the precipitated fatty substance is extractedwith ether and the ether is dried with calcium chlorid. Afterevaporation of the ether a dark colored thick oilremains. It isdissolved in warm petrol ether and the resulting solution is ei aporatedin vacuo and by being left for some time in cacao, the petrol ether canbe entirely removed from it. A semi-fluid brownish product resultscontaining about 10 to 11 per cent. arsenic and Oto 7 per cent.

chlorin. It is insoluble in water and soluble in the usual organicliquids e. g. alcohol and ether.

In order to prepare the strontium salt the product is dissolved inalcohol and poured into a well cooled solution containing an ex oess ofstrontium chlorid in methyl alcohol, through which ammonia gas is beingpassed.

A heavy amorphous precipitate of a slightly brownish color separates,which is collected on a filter and carefully washed'with alcohol. Afterdrying the salt forms a flesh colored tasteless powder. insoluble inwater and containing essentially about 12 per cent. of arsenic. Thecalcium salt has essentially the same properties.

Example 2: 10 parts of behenolic acid and 15 parts of arsenic trichloridareheated for 6 hours to 140 0.. The resulting product is less coloredthan the corresponding stearolic acid compoundand is isolatedin the sameway as the latter product. It is finally obtained as a light brown thickoil containing about 15 to 15.5 per cent. of arsenic and 5-6 per cent.of chlorin. On allowing the oil to stand for some time unchangedbehenolic acid separates in crystals. The oil after being separated fromit contains a higher percentage of arsenic. This separation can also beeffected by solution in a small quantity of alcohol and strong coolingof this solution.

The strontium salt is prepared as described in'Example 1, and forms analmost colorless, tasteless powder containing about '12 to 1 k per cent.of arsenic.

Example 3: 2 parts of behenolic acid and -5 parts of AsBr are heated for14 hours to 120140 O. The product of the reactionis a dark colored-thickoil. It is worked up as described in Example 1. product is a semi-solidbrown substance containing bromin and a few per cent. of arsenic.

1. The herein described new high-molecular fatty acid compoundscontaining arsenic and halogen, which in the acid form are semi-fluidbrownish compounds practically insoluble in water and solubl'einalcohol, forming salts with metals which retain the valuable therapeuticproperties exhibited by the acids, substantially as described.

2. The herein described new high-molecular fatty acid compoundscontaining ar- The resulting senic and chlorin, which inthe acid formare semi-fluid brownish compounds practically insoluble in water andsoluble 1n alcohol, forming salts with-metals which retain the valuabletherapeutic properties exhibited by the acids, substantially asdescribed.

3. The herein described new product being a stearolic acid compoundcontaining arsenic and halogen, which is in the acid form a semi-fluidbrownish compound insoluble in water and soluble in alcohol and ether,forming metal salts which retain the valuable therapeutic propertiesexhibited by the acid, substantially as described.

4:. The herein described new product being 'a A stearolic acid compoundcontaining arsenic and chlorin, which is in the acid form a semi-fluidbrownish compound insoluble in water and soluble in alcohol and ether,forming metal salts which retain the valuable therapeutic propertiesexhibited by the acid, substantially as described.

In testimony whereof I have hereunto set my hand in the presence of twosubscribing witnesses.

EMIL FISCHER.

Witnesses HENRY HASPER, ARTHUR SCHROEDER.

